Long Legs And A Short Skirt
by haunted-mind-14
Summary: Slash! Dean Ambrose/Jonathan Good and Seth Rollins/Colby Lopez pairing. This story contains cross-dressing. AU. Halloween! Jon and Colby are attending a costume party, Colby dressing in drag. "But for a boy to look like a girl is degrading, 'cause you think that being a girl is degrading. But secretly you'd love to know what it's like, wouldn't you? What if feels like for a girl."


Author's note: This is my attempt to do something different!

Summary/things to explain before you read. In this story Jon and Colby aren't wrestling. This is an AU story set in the year 2007. Jon and Colby are college students in Iowa, ages 21 and 20, respectively. They both live with Colby's family. They took Jon in after Colby befriended him freshman year of high school and found out about how horrible his home life was. Going for what's been established in Jon's wrestling promos, that his dad isn't around, his mom's a whore and a junkie, etc, just in general that he had a bad life and they wanted to take him in and help him out.

Our boys have big plans to go out to a Halloween party. Somehow the idea is thrown around that the men should cross-dress for the party as their Halloween costumes. Colby is enthusiastic about his idea. And the hilarity ensues. Told from Colby's POV. Also included in this story is Marek Brave, an indy wrestler and friend of Colby's. Just a small role.

While writing this, I listened to the song "Damn, I Wish I Was Your Lover" by Sophie B. Hawkins on repeat. I included at the beginning the intro to the Madonna song "What It Feels Like For A Girl". It's an excerpt from a movie made in 1993 called "Cement Garden".

I hope you guys like this story. I think you'll find this to be very different from my other Ambrollins slash story. Hopefully I don't make anybody cry with this one. To be honest, after finishing Feel Again I needed something like this as sort of a change of pace. Trust me, no sad ending here. Just have fun with this. Some cute, tongue in cheek, sweet Ambrollins love. Enjoy!

"_Girls can wear jeans and cut their hair short. Wear shirts and boots. 'Cause it's OK to be a boy. But for a boy to look like a girl is degrading, 'cause you think that being a girl is degrading. But secretly you'd love to know what it's like, wouldn't you? What if feels like for a girl..._

_Three days before Halloween..._

The cool temperature of the cement felt good against my backside, almost refreshing. October was one of my favorite months. It fell right before the big holidays of the year so you could enjoy it, you weren't too busy hurrying around trying to stuff a bird or find the perfect gift for your aunt Sheila who you only saw once a year on Christmas. There was just enough warmth in the air that you could spend a sunny day outside and not have to be constricted in layers of fabric. There was just enough of a chill at night that you needed to wear a sweatshirt when you went to the high school football game on a Friday night. It was also a month of change, one that fell during the transition of seasons. It made you feel alive.

I felt alive as I sat on the back steps of my parent's house and watched Jon as he smoked a cigarette. I didn't smoke, I didn't like the fact that he smoked. I loathed the smell and hated the idea of the adverse affects it would have on his health later on in life, but there was something undeniably sexy about it. Could it have been the way he gripped the butt with his thumb and forefinger as he took drag after drag? Maybe it was the satisfied look on his face as he got his fix of nicotine? I decided, as I watched him, it was the fact that every time he placed the end of it between his lips, I imagined it was my penis instead of a cigarette.

"I got your fake ID today." he told me as he stomped out the end of his smoke and reached into the pocket of his jeans. His words brought me back to reality and away from my erotic fantasy.

"Yeah?" I asked him, excited to finally see it. Jon and I had plans to attend a costume party for Halloween at a local bar. He was already twenty-one. I still had months to go before my twenty-first birthday. Jon assured me a couple of weeks ago that he would take care of me. When Jon tells you he's going to do something he does it, no matter how many hoops he has to jump through.

"It looks _sort of_ like you..." he mumbled as he handed me the card. "You'll be dressed in drag anyway, so it doesn't really matter..."

I laughed. "Yeah. I guess not." I giggled as I took my new identity from his grip, our fingers brushing together as I did. "Connor Lee?" I asked as I peered at him.

"At least I got you the right initials?" he grinned. "You're now a twenty-four year old."

"Thanks, Jon." I smiled as I wrapped my arm around him, my cheek resting on the shoulder of his leather jacket.

"Hey, no problem. I wouldn't want you to have to sit at home while the rest of us go out and party for the night. It's gonna be the witching hour, the devil's playground, the demon's night..." he teased me as he wiggled his fingers creepily in front of my face. We both laughed. I got so lost in the moment that I forgot I was still leaning against his shoulder. I decided to stay put. If he wanted me to move, he'd let me know.

Jon was my friend. My adopted brother. My current crush. I met him my freshman year of high school. I'll never forget the first time I walked past him in the hallway. He looked like that boy, the one that every high school has at least one of. The boy who seems mysterious, intriguing, rebellious, smart, broken, sexy, flawed. I know it sounds like a cliché, but he was that boy. The one who you always see wearing the same ripped jeans and worn jacket and you wonder if he has a home or if those are the only clothes he owns. The boy who is smart but never does well in his classes. The boy who walks around in a cloud of mystery. That first day of high school I walked by him and I swear, as he breezed by me in the hall, he looked like James Dean. Later on I would tell him that I thought this and he would laugh so hard he would end up drooling on himself and confessing to me that his sides still hurt even an hour later.

I started talking to Jon at school because I felt like if I didn't I would turn inside out. I knew that I was meant to interact with him for some reason, I was supposed to know him. I was right. Getting to know him those first two months of school, I learned he was both exactly like what I imagined and nothing like what I imagined all at the same time. He told me about his life outside of school and I slowly began putting the pieces together. He apologetically explained to me stories from his past. His mother neglected him. His dad was out of the picture. Jon had taken care of himself for a long time. When living with junkie of a mother became more work than it was worth he left home, living with friends or on the street when the opportunity to crash with a friend didn't present itself.

In all of this, I was amazed how calm Jon was about all of it. He told me his stories with a hint of attitude that told me "Yeah, I'm a little different. I didn't grow up like you did. I'm flawed, but in the best way. The way that makes you learn and makes you stronger for having survived it. I'm going to tell you my story and if you don't like it then you can go fuck yourself.". I respected Jon. He came to be my closest friend. We spent any free moments of the school day together.

December of my freshman year Jon told me he had been sleeping in an abandoned building for the last week. I knew right then and there that he'd be coming with me. I'd told my parents select details of Jon's life, but never the whole story. When I finally did they insisted that he come live with us. Just before Christmas that year Jon moved into our house. It was just like having another brother. Now I had three siblings instead of two. It felt good, having Jon with us. It clicked. He was part of our family.

"You sure you want to go through with it?" he asked.

I moved from his shoulder finally, looking at him. "With what?"

"Cross-dressing? Whose idea was this anyway?" he asked, letting out an amused giggle at the idea of Marek and I dressing up as women for Halloween.

"It was our sister's idea. She thought it would be cute if we dressed as ladies and she dressed up in a suit and pretended to be a man." I laughed as well. I had to admit, it made me just a little nervous. There was so much detail that went into transforming into a woman, it was a lot of work. I was still looking forward to it, just for the night. I'd be a liar if I said that I wasn't excited. "We're going shopping for clothes and makeup and wigs tomorrow." I told Jon.

"What about...underneath?" he asked me, his eyes lowering to my lap.

"Are you asking about my junk?" I questioned him, my face twisting as I did.

"Drag queens tuck, you know." he laughed.

"NO. I'm not doing that." I yelled.

"Okay, okay. Don't get offended, princess." he backed away from me as I raised my fist at him. "You don't have to tuck. That's not really what I was asking. I meant...like...underwear. I mean...you have to wear a bra if you're going to have tits. And what about panties?"

I felt my face turn red. I tried to hide from him the fact that asking about what I was going to wear underneath my girl clothes at the party both horrified and excited me. "I...I didn't really think about that part..." I mumbled as I covered my face with my hands.

"Maybe I should go with you." he commented. "I don't want to be seen out with some badly dressed hussy..." he joked with me as he stood up.

"HEY!" I yelled at him. He smiled down at me as he offered me his hand. I took his palm in mine, Jon pulling me up to my feet. "I have good taste." I said, my hands on my hips. "I'm going to be the classiest girl at that party. You'll see." I smiled sweetly as I watched his blue eyes dance in the faint light of the sunset.

"Classiest? More like ASSIEST." he remarked as he leaned down and peered behind me.

"That's it!" I yelled at him, grabbing him and trying to shove him back. It was easier said than done, Jon was taller and bigger than me.

"Calm down, Colby." he told me as he tried to fight me off. "I'm just saying, some guys like a girl with a little junk in the trunk. You got a little booty going on back there..." he laughed as he struggled with me.

"Since when are you checking out my ass?" I laughed even though I regarded it as a very serious question.

"How could I not notice?" he told me softly as he stared down, directly into my eyes.

I laughed as I finally got the better of him and managed to pick him up and carry him far enough to dump him in the pile of leaves my parents had raked earlier. Jon held on as I dropped him and we both fell with a big _whoosh_ into the mountain of multi-colored leaves, that distinct crunching sound crackling beneath us as we laughed our asses off. I looked over at Jon and took a moment to appreciate how sexy his face looked when he laughed and smiled. His dimples were the cutest thing. I wanted to press my lips to them every time they showed. Feeling bold for a split second, I reached over to his face and gently plucked away the few leaves that were stuck to his coif of dirty blonde hair. He continued smiling at me as I did, a positive sign in my book.

There was no way to understand how my crush on Jon had started. I'd probably always had it, just not understanding what it was or what it meant. I felt it truly come to the surface when I started college. I mourned the fact that I didn't get to see him as much, Jon working a full time plus job while I spent three days a week at college. We'd see each other at home, but it didn't quite compare to how we'd spent every day together in high school. During this time, I started to imagine what Jon and I would be doing if I wasn't attending school and he wasn't at work. I was both turned on and surprised when my daydreams turned into fantasies. I started wishing he and I had a sexual relationship. Again, I started feeling that if I didn't do this with Jon, I would turn inside out. I had no idea if Jon was bisexual as well. I didn't really want to ask, the answer intimidating me.

I plucked the last stray leaf off of Jon's face and slowly replaced an out of place strand of his hair, basking in the way it felt so soft between my fingers. All of a sudden I watched as his face changed and I started to worry I'd done the wrong thing. "Oh my god, Colby!" he whispered. "THERE'S A SPIDER ON YOUR FACE!"

I jumped up, causing a ruckus of dry leaves to scatter all over the yard. I yelled and swatted at my face, trying to shoo the spider off. I did this for a good minute or so until I realized that Jon was still lounging in the leaves, laughing his hardest as he watched me.

"SONOFABITCH!" I yelled at him as I slowly realized there was never an arachnid on my face at all.

"What are you boners doing out here?" my sister Amy yelled at us from the back door. "Mom says to be quiet." she told us, sticking out her tongue. "MOM! THEY MESSED UP THE PILE OF LEAVES!" she yelled back into the house, busting us both.

"Your turn." I told Jon, offering him my hand. I pulled him up and helped him to his feet. "We better go get the rakes..." I mumbled. "Right after you apologize..."

""Kay. I'm sorry you're so gullible..." Jon teased.

"You're such a dick." I told him, elbowing his ribs.

"Yeah...I'm a dick." he told me, walking in front of me. "But you love me." he smiled as he stared at me.

XxXxXxXxXxXx

_The next day...two days before Halloween..._

Somehow as I lay in bed last night I decided that if I was going to cross-dress, I was going to be a slutty girl. I dangled in front of me a short blue striped mini-skirt and gave it a serious thought when I heard Jon's voice close behind me. "That's hideous." he whispered.

"It's not that bad." I frowned.

"This is more like it." he smiled, holding up a slightly shorter version of my choice in candy apple red. "I think this is the one." he told me as he took the blue skirt out of my hand and replaced it with his choice. "You need a shirt..." he mumbled as he wandered over to the racks on the other side of the store. I watched his carelessly sexy walk as he moved on and searched for something else to wear that would complete my Halloween costume. I was confused as to how this had become a shopping trip so that Jon could pick out my clothes. All of a sudden it felt like a light bulb went off over my head. I grinned like the Cheshire cat as I walked over to him.

"Here. You hold this, and keep looking for a top for me to wear." I told him as I gave him the red skirt.

"Where are you going?" he asked me, perplexed.

"I'll be right back. I just remembered, I have to go look for something else." I told him, winking at him. He rewarded me with a slightly confused look and a raised eyebrow.

I wandered to the other side of the mall and found the lingerie shop. I felt out of place immediately. 'It's fine. Men come in here all the time to buy things for their women. It's normal.' I assured myself as I browsed through rack after rack of bras and panties. I had no idea what I was doing. My palms began to sweat when the cute girl behind the counter asked me if I needed any help. She had no idea. I politely told her that I was just looking as she smiled at me. I finally found what I wanted. The perfect matching set with a soft pink colored lace padded bra and frilly lace panties. I gently ran my hand over the inside of the bra's cup, not remembering any bra that I'd ever taken off a girl being this soft.

I began to regret my decision to wear ladies undergarments when I came to the horrifying realization that I couldn't try on my selection. I shifted my eyes back and forth, making sure that there was nobody around. The girl behind the counter was busy waiting on some women at the register. Good. I ducked behind a display adorned with panties, every color and pattern you could ever imagine. I used the mannequin dressed in a silk babydoll nightie for cover as I slowly reached around myself and tried like hell to figure out how to latch the bra around my back so I could see how it fit me. "Shit..." I hissed out as I couldn't affix the latch. "How do girls do this?" I asked myself softly.

"Sir..." I jumped at the sound of her voice, the store clerk smiling at me as I slowly turned around. She laughed as she held her hands behind her back. I laughed as well and explained to her that this was to be part of my Halloween costume, as I was hoping to go all out with the cross-dressing idea. Luckily, she didn't kick me out of the store. She smiled sweetly at me and helped me find the right size bra to fit around my muscular chest. I tried on the panties over my jeans and thought they'd be just right once I had no other clothes on.

I thanked her for helping me as she started to ring up my purchase. "You're going to need these." she told me as she held up a very sophisticated looking package of silicone bra inserts.

"Increase your bust size by two sizes..." I read the line on the package out loud, blushing as I did.

She laughed at me. "You were probably going to use socks or tissues, weren't you?" she asked me.

"Yeah..." I said softly.

"These are much more realistic." she promised me. She looked around, telling me "My boss is on her lunch break, she'd kill me if she caught me. I'll sell you two pair for a reduced price." she offered. "You'll have a fabulous set of fake tits." she laughed, putting the silicone gel inserts inside the bag with my bra and panties.

"Thanks." I laughed.

"Anything else?" she asked, smiling at me.

"Yeah...there is something else..." I said.

"Where did you go?" Jon asked me when I returned to the clothing store.

"Just went downstairs to get some other stuff." I mumbled.

"Whatever." he told me, shoving the clothes at my chest. I looked over what Jon picked out for me. The bright red mini-skirt from earlier. A pink and white lace tank top, low cut. A light pink cashmere off the shoulder sweater with three-quarter length sleeves.

I smiled up at him. "I thought you said you _didn't_ want me to look like a hussy..." I joked with him as we walked up to the register.

"Look...if you're going to party with me then you need to look the part. I need you to resemble a girl that I'd hang out with..." he explained to me as he wrapped his arm around my shoulder.

"A slut?" I ribbed him. I earned a heated stare from him as I payed for my clothes. "Being a girl is expensive." I commented as we walked down to the shoe store.

"Nobody said cross-dressing was easy, now did they?" he asked as he laughed.

We met up with my sister outside the shoe store, a tuxedo hanging over her shoulder. "Damn, sis. You're going to be quite the gentleman." I told her as I tugged on the plastic cover of the suit.

"Don't touch it, Colby." she told me as she swatted my hand away. "I have to return it just as I got it." she frowned. "Are you ready yet?" she asked, looking between us.

"I gotta get some shoes." I told her as I pointed to the shoe store.

"Whatever. I'm going to the costume store to find a wig and a mustache. Wait outside by the car when you're done, boners." she told us, walking away. I loved my sister. She was older than me by three years and could be annoying at times, but she was always willing to join in with us when she knew shenanigans were afoot.

Never before in my life had I given so much thought to what a girl goes through. Men just throw on whatever is within reach, clean or not. There's not much thought that goes into getting dressed or doing their hair. Most men have that "I don't care, I'm too fucking cool to care how I look..." attitude. After this shopping trip, I truly appreciated the amount of effort most women put into their appearance. The choices in wardrobe alone were exhausting. I must have tried on ten pairs of heels. None of them were right. I sighed, looking over at Jon. He seemed bored out of his mind.

"Just pick out some shoes, Colby. They're all the same." he told me as he stared at the ceiling.

"They aren't _all_ the same, Jon." I said. "I can't find the right pair."

"Ugh." he groaned as he got up, the jerky movements of his body as he walked away intriguing me to no end. I stared at the wall of shoes and scratched my head. This was a hard choice.

"Here." Jon told me when he returned, tossing a shoebox at my feet. "Try them on. It's the biggest size they have."

I looked up at him and then down at the box again, scared to open it.

"Go on." he told me, his eyes wide.

I opened the box slowly, not sure what I was going to find inside. Jon picked out for me a pair of shiny black leather go-go boots with three inch heels that laced up in the front. "Jon, I can't wear these..." I told him, in awe of the pair of hooker boots he'd picked out for me.

"Just try them on." he urged me as he smiled. "You wanna dress the part or not?"

I sighed as I sat down beside him on the wooden bench that went down the middle of the aisle. I loosened the laces and slowly placed my foot inside of them, delighting in the smell of the brand new leather boots. Son of a bitch. They fit like a dream. I glanced over at Jon. He had a huge grin plastered across his face. "You're really having fun with this, aren't you?" I asked him as I laced them up.

"Not as much fun as you're going to have on Saturday night." he grinned. "They fit?"

"Yeah." I said softly. "They fit." This pair of boots he'd picked out for me was perfect. They were impossibly sexy and over the top. Just what I needed to complete my outfit.

"Let's go then!" he said, standing up quickly. "I'm starving."

Jon and I stopped at the food court after we left the shoe store. "You wanna share one of those humongous chocolate chip cookies with me?" he asked as he nudged me.

"No, you go ahead. None for me." I told him. He glanced over at me, frowning. "What?" I asked him. "I have to watch what I eat. I don't want my ass to look all fat and lumpy in that mini-skirt you picked out for me..." I joked.

"You're an ass." he giggled.

XxXxXxXxXxXx

_Saturday...Halloween night..._

"Don't move, Colby. You're going to get your ear burned!" my sister yelled at me, doing her best to avoid charring my earlobe with her hair straightening tool as she passed it through my locks of long black hair over and over.

"Sorry, sis." I mumbled.

"You should have just bought a wig like I did, dumb ass." Marek told me, grinning as he leaned over in front of the mirror and secured his curly platinum blonde wig to his own hair.

"Okay, Marilyn...I'll remember that for next year..." I joked.

"Hey, yeah. I've adopted a girl name for the night. You need one too." he told me as he sat down on the bathroom counter.

"Shit. Fine...I'll be known as Colleen for the rest of the night." I said triumphantly. Marek, Amy, her friend Sarah and I all gathered in the biggest bathroom in the house just off my sister's bedroom to get ready for the night ahead. Amy straightened my hair while Sarah painted my face with seemingly endless layers of makeup and mascara. "I'm totally going to have a five o'clock shadow before the night is over." I laughed as Sarah applied blush to my cheeks. "My facial hair grows in fast."

"The makeup should cover it." she laughed. "At least for the party."

"Damn, you gotta shave your legs, son." Marek laughed as he pointed to my legs.

"Oh, shit." I said. "I hadn't thought about that. I can't walk around in a mini-skirt with these hairy legs." I grabbed a razor from the sink and began running it up my leg, horrified when both girls started shrieking in unison.

"COLBY! Holy shit. You can't do that. You're going to get razor burn!" Amy yelled at me. "You need shaving cream." she laughed. "You don't shave your face without it, do you?"

"No, I guess not." I said, embarrassed. When the girls were fully satisfied with my hair and makeup job, Marek took his turn in the makeup chair as I sat on the edge of the bathtub and turned on the hot water, lathering up my legs so I could shave.

"I can't believe what I'm seeing." I heard Jon say. I turned around slowly, glancing at him over my shoulder and then returning to my job.

"I gotta have smooth legs if I'm gonna rock that skirt I bought." I told him.

"You're gonna have to shave your chest too. Probably better get those arms done, while you're at it. And your armpits..." Amy yelled from the bedroom.

"Shit..." I said, the fact that I hadn't thought of any of those things sinking in as I rinsed off my left leg and started in on the right.

"You missed as spot." Jon joked as he sat a beer down beside me.

"Kiss my ass, Jon." I said as I grinned and pointed the razor at his nose.

He leaned close to me, nearly making me jump out of my skin as he told me "You look pretty enough tonight and I just might...", licking his lips as he turned away. I started to feel dizzy. Had he really just said that? I steadied myself on the side of the bathtub with one hand and grabbed my beer with the other, taking a long drink out of it.

"Do I look pretty?" Marek sang out in a high pitched voice, turning around in his chair so I could see his made-up face.

"Pretty horrible..." I laughed.

"You know what, fuck you, Colleen." he insulted me.

"HAH! COLLEEN?" I heard Jon laughing from the bedroom.

"Look, we can't both be the pretty one..." I said as I batted my eyelashes and pushed my lips out. Marek laughed and tossed a towel at me, nearly causing me to fall into the tub.

Once I was sure that I was hair-free in all the right places I fetched my bag of clothes and the box containing my go-go boots. "Damn, how do girls do this?" Marek asked as he tried to pull on a pair of pantyhose.

I couldn't resist the urge to laugh. "You look so ridiculous right now." I giggled as I watched the confused expression on his face.

"AMY! I need help!" he yelled, laughing when he looked at me to see I was still laughing. I stood up and stared in the mirror, amazed at what I saw when I took a long look at my reflection. My sister had done an amazing job of straightening out my usually curly, unruly mess of hair. It fell just right, over my shoulders. I reached up and ran my hands through it, astonished at how soft it felt and how it shined as it hit the light. I looked nothing like myself. My eyes looked bigger and brighter with the addition of eyeshadow and mascara. I stopped staring at myself long enough to look at the reflection behind me, seeing Jon helping my sister put her tuxedo on. I smiled, a sudden warm feeling rushing through my body. He looked over, glancing at me. I grinned for a second and then looked down.

"Where's your costume?" I asked Jon as I turned around.

"It's a surprise. I'll put it on in a few minutes." he said.

"Yeah, Jon. Where's your costume?" Marek chimed in. "Why aren't you cross-dressing with us?"

"I don't think I'd make a very good woman." he laughed. "I'd just be a slutty bitch anyway. Besides, I don't have the delicate features that you and Colleen have, Marilyn..." he said, barely spitting out the words before erupting in laughter.

"Hey, laugh if you want." I told him. "But it takes a strong man who is comfortable and in touch with his feminine side to dress up like the opposite sex."

"I'm sure it does." he told me as he smiled at me once again.

"Colby, go get us a few pairs of your socks." Amy instructed me.

"Why?" I asked her.

"You know, so Sarah and I can have some big ol' man bulges in the front of our pants..." she told me as she moved her hips and pointed to her crotch. We all laughed so hard that I was sure we'd all end up pissing our pants.

I closed the bathroom door and locked it. I pulled my outfit for the night out of the bag, shaking my head as I looked at it all. "Am I really doing this?" I asked myself softly. I stripped down to nothing and pulled the pink lace panties on first, delightfully shocked at how soft they felt against my ass. I pulled them up and ran my fingers along the line of the elastic waist, looking in the mirror and adjusting them so that they sat just right on my body. I shifted my cock a little bit so that it didn't stick out so far, shivering as it rubbed against the soft cotton liner of the crotch. I hated to admit it, but this was starting to be a bit of a turn on for me. A slight feelings of shame and confusion mixed with desire as I pulled the mini-skirt up over my hips. It was impossibly tight, hugging and stretching over my body, the fabric straining against my ass. I pulled it on all the way, flabbergasted at how short it was on me. I was amused to find that if I bent over just enough, you could see the pink lace panties. I took out the other item I'd purchased at the lingerie shop, a garter. I picked out a pink and white lace garter adorned with faux pearls. I pulled it up my leg, setting it in just the right spot. I grinned, thinking about the one person besides myself who I was hoping would see this little piece of lace wrapped around my leg.

Next I strapped the bra on, this time finding it easier to fasten around me. I silently thanked that girl in the lingerie shop for explaining to me how to do it. Taking a bra off of a girl, that was fine. It was much different when you had to put one on yourself. I decided to wait until I was fully dressed to put the silicone gel inserts into the cups of the bra.

I pulled the lacy tank top over my head and again felt a thrill as the soft fabric made contact with my freshly shaven skin. The sensations made my legs shiver, erotic thrills that were all new to me coursing through my body. I picked up my second bottle of beer and gulped down what was left of it quickly. The cashmere sweater was the best part. It was amazingly soft against my skin. The sweater sat just right, falling at my waist right where the short skirt started. If I raised my arms or leaned the right way, my midriff showed out the bottom. It fell just off my left shoulder, showing the spaghetti strap of the tank top and my bra strap.

I was just about to open up the box with my "tits" in it when I heard a knock at the door. "Colb...Colleen...can I come in?" Jon asked.

"Yeah." I answered. I turned around to see Jon standing in the doorway. "What the..." I mumbled softly as I saw his Halloween costume. He stood there in the doorway, leaning against the frame. His dark blonde hair was slicked back against his head. He wore faded blue jeans with a rip at the knee. A tight white t-shirt clung to his body, doing nothing to hide the muscles of his upper body and his arms. He held his leather jacket over his shoulder as he stared at me, a sexy expression on his face. "James Dean..." I said softly. "What..."

"I thought you would get a kick out of it, that's all." he told me as he set his leather jacket down and closed the door behind him. "You look very pretty." he grinned as he walked over to me. I felt my heart start to beat twice as fast as I stared at Jon. I'd never seen this type of look on his face before and it made me want to melt and scream at the same time.

I tried to play it cool by telling him "You look good yourself..." but it just came out sounding awkward and forced. I kicked myself for even trying. Jon didn't seem to notice, or if he did he ignored it. He just kept moving towards me.

"You make a very beautiful woman." he told me, reaching out to touch a few strands of my straightened hair. He glanced at my attire, stepping back to take a look at me. "See. I picked out some good clothes for you." he said as he grinned. "Colby, are you wearing a bra?" he asked me as he reached out once again and tucked his finger underneath the strap of the bra.

"Yeah, I am." I said, swallowing hard and trying to catch my breath. This was closer than we'd ever been, at least in an intimate fashion. I didn't know how to act.

"What are those?" he asked, peering over my shoulder at the box containing my inserts.

I giggled. "Those are my fake tits. I was just about to put them in." I told him, sliding the box across the bathroom counter.

"Can I?" he asked me. I could have died when he asked me that question. I found myself nodding as I squirmed on the inside. I took a deep breath, trying to remind myself that I was someone else for the night. I was Colleen.

Jon opened the box and took out the silicone pads, pressing them between his thumb and forefinger. He poked them and touched them, a smile on his face.

"Jon, stop playing with my tits." I told him, raising my voice so that I sounded like a girl.

"I gotta tell you Colleen, that's the first time a girl's ever told me that..." he grinned, catching his eyes with mine. "Four of them?"

"Yeah. The girl at the lingerie shop wanted me to have nice big boobs, apparently." I laughed.

"So that's where you went..."

"Yeah." I smiled. Jon gently lifted up my sweater so that he could gain access to my bra.

"Pretty pink." he whispered as he exposed the lace undergarment. He pressed two of the silicone inserts together and moved the cup of the bra, opening it up and slowly sliding each one inside before closing the cup back over them. He did both sides, achingly slowly, never taking his eyes off of me. When my tits were in he pulled my tank top and sweater back down, stepping back to take a look at me. "Those are pretty nice tits, Colleen." he smiled. "I just have one question." he said to me as he moved closer once again. "Do the panties match?"

I swallowed hard again. I couldn't answer. He was standing so close to me, I could feel his breath on my exposed shoulder. "I guess if you're not going to answer I'll have to find out for myself, huh?" he told me. He wrapped his arm around my waist and pulled me close, our bodies meeting. He reached down to the back of my skirt and slowly hiked it up, stopping only when his fingertips made contact with the lace fabric that was covering my ass. I gasped when his hand touched my ass, the contact exciting me more than I could ever have imagined it would. "Lace?" he whispered slowly, peering over at me with his blue eyes as he smirked. He leaned in close and pressed his face against my straightened hair, taking in a deep breath. "You even smell like a girl." he murmured. "This is going to be fun." I felt my legs nearly give out and the lights in the bathroom become instantly brighter for some reason as Jon whispered to me.

I was relieved when Jon stepped away, telling me "I'll be right back. I have something for you." I feared that if Jon stood that close to me for much longer I would have passed out.

I stared at myself in the mirror, fully dressed now except for the hooker boots. I turned around in circles several times in front of my reflection, trying to see myself from every possible angle. "Colleen." I said to myself. "You look pretty hot tonight." I took the go-go boots out of the box and put them on, the transformation complete. I had to admit, Jon had good taste. The boots completed the outfit. I was pondering how my feet would feel at the end of the night after spending hours in heels as I heard Jon's footsteps.

"I got this for you." he told me. I watched him as he approached, his hand behind his back.

"What is it?" I asked in a high pitched voice, twirling my hair between my fingers as I did.

He smiled at me, showing me what he'd bought. A single pink rose. I grinned excitedly, taking it from him. "I thought that a pretty girl like you would appreciate a flower before we went out for the night." he told me, smirking sweetly as he watched me rinse out my empty beer bottle from earlier and refill it with clean water so I could use it for a vase.

"Thank you, Jon." I said sweetly in my girl voice. "But I hope you don't expect me to put out later just because you bought me a flower..."

He laughed at me, telling me "Actually...that's exactly what I was hoping.".

I stared at him with wide eyes, trying to read him. I wanted to break character and ask him if he was serious, but I didn't. I decided it would be better if we just had fun.

"UGH?" I moaned, pretending to be displeased. "What kind of girl do you think I am?!" I cried as I walked out of the bathroom, twitching my hips and flipping my hair as I did. I went down the hall to my bedroom, placing the beer bottle containing my rose on the side table by my bed.

Half an hour later we were all in costume and ready to hit the party. We stood in the family kitchen and smiled as out parents shook their heads at us in unison, trying not to laugh even though I know they thought we looked hilarious. "You kids...you have a designated driver, right?" Mom asked us, her hands firmly planted on her hips as she stared at us.

"Don't worry Mrs. Lopez. I don't drink so I'll make sure these kids get home alright..." Sarah joked.

"Good, that means we can start taking shots..." my sister joked. We stood in a circle in the kitchen, clanking together our shot glasses as we downed the first round of the night, Jack Daniels burning his way down our throats as we all smiled at each other. My sister looked butch and then some in her tuxedo and mustache, a scraggly old man wig on top of her head. She looked nothing like a woman.

"I gotta take a few pictures of you kids before you go." Mom told us, running off excitedly to fetch her camera. Dad sat at the kitchen table, cringing at the sight of two of his kids dressed in drag. Marek and I posed and hugged, sticking our fake tits out and pressing our shiny, overly glossed lips together as we postured for the camera. We turned around and shoved our asses out as we peered over our shoulders, barely containing our laughter long enough for Mom to take our picture.

"Colleen, I can see your panties!" my sister howled as I bent over. I acted like I was embarrassed as I quickly covered myself up, tugging my skirt down. I glanced over my shoulder at Jon, a devilish look on his face. Sure that he'd seen what everyone else had I took another shot, a mischievous feeling washing over me as I grinned.

XxXxXxXxXxXx

Of course, the bar was packed. Most everyone else in attendance was also wearing a costume which made me feel instantly better about going out in public dressed in full drag. The bouncer stared at Connor Lee's ID card for a few moments, taking a quick glance between me and the card a couple of times before handing it back to me and telling me to have fun. I looked over at Jon out of the corner of my eye as he flashed me a big grin and shot me a triumphant thumbs up.

There were no other men dressed up as women, at least not as far as I could tell. Just Marek and I. We got the obligatory cat calls and horrible obscenity laden pick up lines as we walked through the crowd and made our way to the bar. "Damn baby...dat ass!" a patron dressed as Dracula commented as we passed by him, swatting at my ass as he licked his lips. On a regular day, I would have cold cocked him. Tonight, I was a girl, and a girl with an ass that men appreciated, apparently. I smiled, covering my face with my hand and tee-heeing as I passed.

I couldn't help but take note of how the skirt felt as the fabric moved over my ass and hips as I walked through the crowd of people. It didn't quite stay put like I had thought it would. I had to pause a few times to pull it down just a little so that I wouldn't risk my ass hanging out of it. What I loved most was how with every step I took I could feel the lace garter rubbing between my legs, brushing against my flesh with every stride I took in my leather go-go boots.

I stood at the bar and made small talk with some of our other friends as we commented on other people's costumes and danced to the music. Jon approached me after a little while, a wide smile on his face as he got closer. He held two glasses in his hand and I began to fear what he might have in them. He smiled at me, pushing one of the drinks into my hand. "What's this?" I asked, staring down into it. It looked like red wine and smelled horrible.

"Devil's blood." he grinned. He took a long drink out of his glass, wiping the red liquid from his lips when he finished.

"What's in it?" I asked as I took another sniff of it.

"Just drink it, Colleen." he frowned, shoving the glass closer to my mouth. I took a short drink, the red liquid burning my throat as it went down.

"Holy shit..." I coughed. It was strong, but didn't taste as bad as I thought it would.

"You want another one?" Jon asked as he leaned on the bar next to me, his eyes drinking me in.

"You're just trying to get me drunk." I teased in my high pitched voice. "Buying a girl drinks won't get you laid. You're going to have to try harder than that, mister." I joked as I poked his chest.

"It's a start, right?" he giggled as he ran his fingertips across my cheek. "I'll get us a couple more drinks." he told me as he breezed off to the other end of the bar. I stared at Jon as he interacted with the bartender. He looked impossibly sexy in his James Dean get-up. What made it even sexier was the fact that he'd done it for me, remembering what I'd told him years ago about my first impression of him. I smiled as I watched him. It started to become unbelievable to me that Jon and I might end up together by the end of the night. I took a deep breath and looked down at myself, remembering that I was dressed up as the kind of girl that Jon liked. I wasn't his friend, his brother tonight. I was Colleen, and I would have him one way or another.

After several rounds of drinks we were all feeling good. We posted up at a table near the DJ booth and laughed as we took shots and danced with each other, all five of us nearly dying of laughter as Marek's wig suddenly flew off during a heated dance with a girl dressed up as Wonder Woman.

A cute young college age boy came over and joined us, sitting between my sister and I as he introduced himself and told us how much he liked our costumes. He was dressed up as a tough biker dude and I had to laugh when he told us that he was gay, the costume looking even more ridiculous on him now than before. Out of nowhere, he put his hand on my leg and bit his lip, winking at me. I felt my body clench as he hit on me. "You look pretty sexy, honey. I wouldn't mind taking you back to my bed later..." he told me, winking.

"I NEVER!" I hollered, swatting his hand away. He laughed at me as he recoiled.

Jon stood up and moved around the table, coming to stand behind me. He pressed his hand to my shoulder and leaned down, telling our new friend, "Sorry, Charlie. This is my girl for the night...", nuzzling my neck with his nose. He pulled out my chair and brought me to my feet, leading us towards the dance floor. The DJ started to play "Spooky" just as we stepped out on the floor. Jon gripped my hips tight and moved to the music with me as the song blared out of the speakers, the lyrics really speaking to me as I listened to them and stared into Jon's eyes. _"Love is kinda crazy with a spooky little girl like you..."._

"Are you having fun tonight, Colleen?" Jon asked me as his face closed in on my neck. "I meant what I told you earlier. You look beautiful as a woman. But, you look even better as a man.", he smiled over at me as he rested his head against my shoulder and danced with me.

"Jon, I gotta ask you something." I said as our hips swayed and our feet moved in time to the music. "Would this be happening if we weren't dressed up for Halloween? Like, you're only doing this because I'm dressed up as Colleen?"

He sighed as he straightened up and stared in my eyes. "I'm getting a thrill out of seeing you dressed up as a woman, yes. It's doing something to me that I can't explain. I'm so into it. Seeing you this way turns me on, I can't hide it. So I guess the answer is yes and no. No in the way that I probably wouldn't be having as much fun with this if you weren't cross-dressing. Yes because I've had a crush on you for a long time now and I've been afraid to tell you."

I felt every bit of breath leave my body with that confession. I calmed myself and played it off, telling him "You like this, huh? You think that me dressed in drag is a turn on? Really?" as I giggled.

"Yeah." he nodded.

"Then I say we have fun with it, for tonight at least. Halloween only comes once a year, right?" I told him as we danced.

He grinned at me and pulled me in close. "I like that idea." he cooed in my ear. He moved his face over and gently pressed his lips to my cheek, giving me a little kiss as the song ended.

XxXxXxXxXxXx

"We're going to stay up all night and watch horror movies!" my sister announced as she bounded in the house. "As soon as I get out of this damn suit..." she slurred out as she fumbled with her tie.

"Sis, you're drunk. Try to keep yourself from waking up our parents, okay?" I begged her as she collapsed on the couch with Sarah.

"You two boners aren't going to stay up with us and keep drinking?" she teased.

"Nah. I'm going to my room." I told her, heading up the stairs.

"Yeah. I'll join you." Jon said as he followed me.

"Whatever. You dicks are acting weird tonight anyway." she slurred as she tried to pick out a good scary movie.

Jon and I walked up the stairs together, the anticipation of what would happen next driving me insane. I jumped as I felt Jon delicately run his fingers up the back of my leg as I climbed the stairs. "I'm glad you shaved your legs. Your skin is smooth..." he said softly. All I wanted to do was make it to my bedroom.

We went inside my room, Jon closing the door behind us. He was still dressed as James Dean, leather jacket and all. I sat down on my bed and started taking off my boots, a great feeling of relief coming over me as I got the first one off and began working on the second one. Jon kicked off his shoes as well and shrugged off his jacket. I leaned back with my arms behind me and my palms flat on the bed as I peered at him. He looked like walking sex in his tight t-shirt and form fitting jeans. "My pretty little Colleen. What was it you said about not being that kind of girl?" he teased me as he stood in front of me. He reached down and picked up my right leg, raising it and tickling my bare flesh with his fingers as he ran them up and down. "Beautiful skin. Beautiful girl. I can see your panties again, honey." he told me.

"You saw them earlier, didn't you?" I asked as I felt my skirt begin to ride up my hips.

He smiled at me as he pushed his hand up my skirt, telling me "Yeah, I did. I was surprised. It was pretty sexy, seeing you bend over and flash me a look at those pink panties.". I smiled up at him as his hand moved over my thigh. He switched legs and lifted up my left leg, my red skirt creeping up further as he leaned down and kissed me from my ankle to my knee. He slowly moved his hand up my left thigh and stopped abruptly when his hand crossed over the garter. "What is this?" he asked, a cunning look on his face.

"That's a surprise." I whispered as I leaned forward and touched his face.

"You were just waiting for me to find that garter, weren't you?" he asked softly as he ran his fingers over the lacy fabric. "I'm going to save that for later." he told me as he pulled me up off the bed. "Long legs and a short skirt..." he whispered as he ran his hand down the length of my body, starting at my neck and ending right where the mini-skirt ended.

"Am I the kind of girl you like?" I asked him in my girly voice.

"You sure are, baby." he said as he pulled me to his body. He gently brushed my long hair away from my face and neck, tucking the straightened strands behind my ear. Jon pressed his mouth to my neck and let out a small guttural moan, his lips moving across my skin and leaving a trail of wet kisses behind as he did. I moved his t-shirt up and gently touched his abs as he continued kissing my neck and exposed shoulder. "I've been wanting to do this all night." he confessed to me. "Actually, since before tonight...".

I smiled at his words, moving my hands up his shirt more and more. "I wanna see how you look in just the bra and panties..." he told me as he looked in my eyes. Jon pulled my sweater up over my head and then removed my tank top. "You're such a pretty, slutty little girl." he remarked as he moved his fingers over the elastic strap of the lacy bra. "You probably love bad boys like me, don't you?" he asked me, glancing at my face.

"I love them." I said in my girly tone. It hurt my throat to keep talking like a girl all night, but if it meant that we kept up the little gender swap charade we had going on between us, then I was all for it.

"I wanna take that tight little skirt off next. I can't wait to see what you've got for me inside those cute pink panties." he whispered in my ear as he coaxed his fingers inside of the band of my mini-skirt. I moaned with delight as his hands made contact with my stomach. He pulled down my skirt slowly, pushing it down over my hips and letting it drop down to my feet with a soft "whoosh". He grinned at me, a sexy look in his eyes as he took my face in his hands. He kissed me and I jumped inside at the sensation of how soft his lips felt as they brushed against mine. Jon's kiss tasted like devil's blood and cigarettes, the most intoxicating mix of flavors. I pushed my tongue over my lips and across his, into his mouth. His hips pushed forward and met with mine as our kiss grew into something faster and deeper. I could feel my cock beginning to stiffen against the lace front of the panties, my balls starting to swell so much that I thought they might escape out the sides of the garment.

Jon pushed me down to the bed eventually, removing his shirt and throwing it aside before slowly climbing on top of me like a wild animal that was sizing up it's prey. He straddled me and I could feel his cock through the denim of his faded jeans, straining against my leg as he hunched over me. He reached over me and grabbed the rose he'd given me earlier, plucking it from the beer bottle and holding it over my body. "Such a pretty little slut." he said softly as he moved the bud of the rose over my bare skin, the soft petals tracing across my collarbone and my chest. I closed my eyes and tried to steady my breathing as my desire began to grow for him. Jon ran his hands over the fake breasts jutting out of my chest, gently laughing as he squeezed each one in succession. He reached inside my bra and took the silicone inserts out, throwing them on the floor. "We don't need those." he told me. He walked his fingers down the length of my body and stopped when he reached the pink lace panties. "This is what I've been waiting for." he told me as he ran his hand over the lace. I moved my hips off the bed with the touch of his hand so close to my cock, the thought of him touching me there more than I could handle.

"Jon..." I whispered as he moved his hand over my covered cock, the softness of the lace and cotton as it rubbed against my fully engorged genitals an incredibly dirty feeling.

"You like that, baby?" he asked me as rubbed again, taking my cock in his hand through the material. He rubbed it up and down until a small wet spot appeared on the panties, my pre-cum soaking through the fabric. "I don't know who likes it more, you or me." he quipped as he helped me sit up. I sat up in bed as I watched his face. He moved my hands to the button of his jeans. My hands couldn't move fast enough as I fumbled to undo the top of his pants. I finally did and moved then down his hips just enough to free his cock from his clothing. It popped out, springing to life as it appeared before me. I moved my hand up and down his length, his cock smooth and thick. It was just how I'd imagined it over and over again in my mind. I used my thumb to tease the head of his dick as I moved my palm over it, spreading his pre-cum that had leaked out over his bulbous head. Jon sighed and tossed his head back, moaning out in pleasure with my hand on his cock.

Jon pushed me back down against my bed, moving down with me and kissing my stomach. He reached up and moved the bra up, exposing my nipples. We rubbed our erections together as he started licking and biting at my now exposed nipples. I writhed in ecstasy as he gently nibbled on the sensitive nubs on my chest and as his hard cock moved against mine, against the lace of my underwear.

Jon moved down my body and stopped again at my panties. He kissed my body just above where the elastic band of my underwear rested against me. Then came what it seemed like I'd been waiting all night for. Jon pulled the pink lace panties down. I lifted up my legs and separated my feet just enough for him to pull them off my body. My cock stood straight up once it was released from the restrictions of the panties. He smiled down at me and winked as he dipped his head down to my thigh. He kissed the now smooth skin of my shaved leg as he closed in on the garter. "This really was a nice touch. I wasn't expecting it." he told me as he ran his fingers between my body and the garter. "It really completed the fantasy for me." he said as he played with the lace and pearls, twisting the little accessory between his thumb and finger. He reached down with his mouth and gently took the garter between his teeth, guiding my leg up with his hands as he pulled it off my body using only his mouth. He set the garter down on the side of the bed and stared down at my cock, his eyes closing in on it.

I arched my back and reached behind myself, removing my bra and tossing it over the side of the bed. I took a deep breath and attempted to gain some composure as Jon's face got closer and closer to my cock. "You have a big cock." he commented. "I don't see how it stayed in those little lace panties all night..." His face was almost touching my dick, I squirmed a little as I anticipated the feeling of his mouth on me. "I've been waiting all night and then some to taste you." he told me as he looked up at me with those big eyes of his. He stuck his tongue out and licked at the head of my cock, an acute moan escaping me with the contact. I hissed with pleasure as he started moving his head up and down, the heat and moisture of the inside of his mouth as it closed over my cock the most intensely erotic delight I'd ever experienced. I couldn't help but buck my hips as he started to speed up his efforts. I could feel his chin against my balls each time he took my cock all the way down his throat, my hands clenching the sheets as waves of electricity moved through my spine.

"Jon, you're going to make me cum." I warned him as he increased his suction and moved his mouth faster.

He released my cock just long enough to flash me a toothy smile, telling me "That's what I was hoping for. Give it to me, baby." before going right back to sucking my dick. I cried out as Jon slowly pushed one of his spit coated fingers inside of my ass, bringing my orgasm even closer. I didn't last long once he added the stimulation of his finger gently playing with my asshole. I groaned as I shot off inside of his mouth, his tongue teasing my head with hard flicks as I rode out my orgasm.

I switched positions with Jon on the bed and found myself on top of him, looking down into those dreamy blue eyes. I bent down and kissed him, the taste of my cum mixing in our kiss as he drove his tongue into my mouth. As much as I loved the texture of his lips against mine I broke our kiss rather quickly to move on to the one thing that was on my mind. Getting him out of those jeans. I moved them down his body slowly, remarking as I did, "I didn't even notice when I first unbuttoned your pants that you weren't wearing any underwear...". I grinned as I took off his pants, teasing him "You're just as much of a little slut tonight as I am.".

I put two of my fingers inside my mouth and got them nice and wet. I played with the entrance of Jon's ass slowly until I could push both fingers inside of him, taking it slow. "Fuck. That feels so good, Colby." he told me as he pulled at my hair. I grinned and continued pleasuring his ass. I waited as long as I could before the urge to suck his cock was uncontrollable. I took the big head of his cock in my mouth and sucked on it hard, tasting him on my tongue for the first time as I did. Jon's body responded so well to my activities, his hips moving to meet the actions of both my mouth and my hand. Jon's cock was thick and I loved the fact that sucking at his length was actually making the sides of my mouth sore as time went on. I began using my hand to work up and down his cock, Jon letting out moan after short moan as I did. I knew he had to be close to orgasm. I pushed my fingers inside of him and held them there, using them to play with his prostate as I jacked him off. He let out a loud cry as I did, his face contorted with pleasure. I continued until his cock spurted, leaving cum across the lower part of his stomach. I smiled up at him as I leaned over his body and licked up every drop of it. I sucked his cock up and down a few more times just for good measure, just to be sure that I'd gotten all of him.

XxXxXxXxXxXx

_The next morning..._

I woke Sunday morning to find that I was in bed alone. I rolled over and rubbed my eyes, trying to make everything come into focus. I glanced over at the floor, seeing the pink bra and smiling. I sat up in bed and stretched my arms over my head. I looked over at the table and noticed that Jon had put my rose back in the beer bottle. I stood up and took it out, taking a long sniff of it.

I went to the bathroom and washed off any remnants of the makeup from last night. I slowly made my way downstairs, pausing in the foyer to grab a few pieces of leftover Halloween candy that Mom had left there. I went to the kitchen and found Jon there. He was seated on the kitchen counter sipping a mug of coffee. "Hey. There she is. Prettiest girl I've ever seen." he told me.

"I thought maybe you'd left last night without saying goodbye..." I joked in my girly voice. We both laughed. "Seriously, though." I said as I stood in front of Jon, my hands resting on his thighs, "Next year you're dressing as a woman. I've got it all figured out. We're going to get you a red wig. A little black dress. A pair of skimpy little red lace panties and a matching red bra..." I joked.

"A redhead?" Jon said, making a disgusted face. "I'm meant to be a blonde, baby." he told me as he leaned in close to me.

"What are you dildos doing?" Amy asked us, surprising the both of us with her presence. "You're both blocking the coffee maker. MOVE."

We got out of her way, sure that she had a horrible hangover. "So what did you dicks do last night?" she asked us once she'd satisfied her caffeine craving.

"Nothing..." we both answered at the same time., giggling.

"OH, WHATEVER!" Amy yelled as she stomped away. "I swear to god, you guys should be gay together. You're so weird sometimes..."

Author's note: There it is. I hoped you guys liked it. Let me know what you think?


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